Date: Sun, 17 Jan 2016 02:22:58 +0000 (UTC)
From: Jack Notmyrealname <jacksta@ymail.com>
Subject: Perfectly, beautifully unapproachable 5

Hey readers!  My name is John, if you're my parents or teachers.  If you're
my friend, I'm Jack.  This story is partly true.  All the stuff about
masturbation is anyway.  But the part where I lost my virginity... that
hasn't happened yet.

If you want me to keep writing this story, or write another one, or tell
you more about myself, or just want to talk, email me at jacksta@ymail.com.

Perfectly, beautifully unapproachable
5. Bicurious II

Having two sessions with Sam a week was still odd to me.  Just one day
after having sex with her on Tuesday, I was already planning out jerking
off the right amount of time before our next fuck.  And Thursday morning, I
put aside the time to jerk off before school.

The day went much better than Tuesday.  I actually caught some of the
things the teachers said today!  Though not everything.  Turns out that
getting pussy just made me think about it more, not less!

Finally, the end of the school day came around, and I hurried off to
James's house.  I found him alone again, this time on the couch, and
dressed.  He looked just a little... sad.  That's something I haven't seen
before.  I sat down on the couch.

"Yo!" I tried to get his attention.

He stayed silent for a minute.

I tried again, "What's up?"

After a moment, he finally responded, "She has a B in science class."

It didn't hit me instantly, because I wasn't thinking about school.  But of
course, officially I was having sex with her as payment for tutoring.
Which I can't really say we've been doing much of.

This meant that she was having sex with me only because she wanted it.  But
before I could enjoy that thought, the guilt returned and it wasn't gonna
leave so easily this time.  There was no good reason anymore why I was
fucking his girlfriend, and that must have really hurt him.

I only responded with, "Oh."

He looked away.

So I had to ask, "Why do you stay with her?"

He sighed, and said, "She threatened to make sure I never get laid again if
I broke up with her."

"How?"

"She said she'd tell everyone I made her do stuff against her will."

I felt worse.  "So no girl would ever touch you again.  In high school."

"If I didn't get arrested."

I spent a moment trying to decide how to react.  I thought I would have
enjoyed this jock who's a big asshole at school feeling this miserable.
But then... she was the bad one.  So I put off my problems with him, and
decided to be sympathetic.  "Fuck, man..."

He laughed quietly.

I moved toward him and put my arm around his shoulder.  We didn't say or do
anything for a minute.

But then my thoughts changed a bit.  "You know, I owe you something..."

He looked at me, and his eyes widened a little bit.

It didn't look like he was going to say anything, so I just went ahead on
my own.  I took my arm off him and reached for his belt loops.  As I
started to push his pants down, he lifted up to help me out.

After pushing his pants with his boxers down past his knees, I looked at
his crotch from this closer perspective.  He was right... the careful
grooming really did make his dick look great.

I reached over and grabbed his dick with my right hand.  I was breathing
faster, and hoped he didn't notice.

I rubbed it slowly and it came to life.  In a moment, he was fully erect in
my hand.  I looked over, and he was breathing harder too.  But he was
watching my hand at this point.  So I kept stroking him.

It was kind of awkward.  I was used to stroking a cock that was much longer
and thicker.  And of course, in my lap, not in the one next to me.
Actually, his size was actually more convenient for this.  It was easier to
make the motion, and with my whole fist around his cock, I could actually
cover the whole length of the shaft with each stroke.  So this is what it
was like for normal-sized guys to jerk off!

I still feel I should point out, he still had a pretty nice size.  Just not
big the way mine is.  My strokes were kinda slow early on, but as I started
to get the feel of the motion at this angle, I started to get faster.

I kept jerking him off for a few more minutes as it got to be more and more
natural to keep going.  He looked very comfortable, and I could see the
pleasure on his face.  But then he let out a small grunt, and I could tell
he was getting close.  So I stopped stroking.

He looked at me with a puzzled look.  "Dude?"

I took my hand off, and when he tried to reach for it, I pushed his hand
away.

See, this was my idea.  I was betting that a jock like him had that
attitude that only sex was worth putting effort into.  That masturbation
was something you did when you couldn't have sex, and only just enough to
get a quick cum.  Which would mean that he would never have edged, or tried
anything else fun that was between just you and your dick.  So I was gonna
show him what a dick is really capable of.

"I know what I'm doing."  I don't know if that was actually a lie.  I
really knew masturbation, but handjobs... not so much.  But it was always
good to let them think I was more experienced than I was.

He just started to lose his erection, and I went back in with my whole
fist, and started stroking him again.

He closed his eyes and quietly said, "Mmm..."

I was getting better at jerking him off, and he was getting more and more
aroused.  He was getting closer to cumming faster each time.  And after
probably a half hour, I had already started and stopped 6 times.

I resumed pumping his cock, and after barely a minute, he was close again.

"Let me cum... please..."

I gave him his wish, and kept stroking. When I thought he was a second away
from cumming, I slowed down a bit to try to stretch out his orgasm.

A powerful orgasm rolled over his entire body.
"aaaahhhhhAAAAHHHHHHHHaahhhhh AHHHHHH!"  Cum started to shoot up straight
in the air.  "Unnhh... UNNHHH... unnhh..." he grunted with his next couple
shots.

After about seven shots, he had his head back, and was panting hard.  I
kept my hand on his dick, and he twitched a couple times as he came down
from his intense orgasm.

I pulled my hand away, and we both looked down.  Cum covered his dick, was
running down his balls, and was splattered across his stomach.  And it was
all over my hand.  So I wiped off what I could on his side.

"Dude..." he started saying.  He was very content, speaking slower than
usual.  "... you are the fucking master."

I just smiled.

"How did you do that?  I've never cummed that hard before," he continued.

I didn't want to ruin it, so I just said, "I guess I'm just the fucking
master."  He didn't really need to know that my hand gave him a stronger
orgasm than a pussy because I put the effort into building it up more than
5 minutes of fucking did.

It occured to him that he should return the favor.  He reached over and
started rubbing my dick through my pants.  I was really tempted to let him
keep going... but I had priorities.  So I stopped him.

"It's my day with Sam."

"Oh, right."  This time, his earlier sadness about that didn't come back.

I was still a little worried though.  "You sure you're ok with it?"

He shrugged, "Yeah, whatever.  It's not your fault."  And after thinking a
bit, he continued, "I'm not gonna stop you from getting laid anyway."

"Thanks."

He stood up and said, "Ima have to fuckin' shower this off."

I had to agree.  There was cum all over him, and it was running down him.
He stripped off the rest of his clothes, and carried them all to his
bedroom.  I heard the shower start.

I looked over and noticed a text message on his phone.  Sam was texting him
to tell me to come to her house.

I walked back to his bedroom and shouted for him, but he didn't hear me.  I
decided I didn't need to be shy here, so I walked into his bathroom and
opened the shower door.

A muscular, naked jock turned to face me.  He didn't need to be shy either!
"What's up?" he asked.

I tried to be specific so he wouldn't think I was going through his phone.
"A message just popped up on your phone.  Sam says she's at her house, so
I'm headed out."

He just said, "So go fuck her!" and turned around to keep washing.  He was
probably just glad she didn't say anything until now!

I left.

At Sam's house, I was surprised to see her mother was home.  When I could,
I leaned in and quietly asked her when we could have sex.

She didn't sugar-coat it.  "My mom's not leaving.  We're just studying
today."

Fuck!  I passed on a handjob so I could... talk about science?  With no
chance of sex?

I didn't think there was any point in pushing the point, so we just got her
school materials out, and we started.  I kept going back in my mind to what
James had said.  She didn't really need these tutoring sessions.  I
wondered whether she had ever needed help... but then again, why would she
have picked me in the first place?  Was it just a joke until she saw me
naked?  But I didn't say anything.

I accepted lemonade from her mother like a dork, and went home.

The next day, I did something foolish.  I forgot my place at school.

I passed James in the hallway.  He was talking with a couple other jocks
whose names I'm not sure I know.

"Hey dude," I said to him.

But he said, "Fuck off."

I stopped and just said, "Huh?"

He reached out and grabbed my shoulder, and shoved me into the locker.  "I
said FUCK. OFF."

I didn't say anything, and quickly walked off.

I hid in the library to think about it.  I felt stupid for not remembering
that he's an asshole.  I had almost forgiven him for everything he had done
to me before!  I still wanted revenge for punching me in the stomach in
underwear after gym class, more than a year ago now.

But I also couldn't deny that he was scared his friends would find out what
we did.  And I couldn't say that it was ok for me to screw up his social
life when he wasn't screwing up my sex life.

After turning things over in my head, I decided to never forget that we
weren't really friends.  Then, I started working on excuses for why I was
going to be late to my next class, on my way there.

My JOB showed up early on Saturday.  I was feeling better since yesterday,
but I was still more glad to see him than ever.  He was more awkward around
me than James, but he never pretended I didn't exist at school.  That was
probably because I was a cool kid compared to him, but I still appreciated
that today.

Besides, my JOB was getting more comfortable around me.  He didn't react at
all when I stripped naked, and we just kept talking.

Soon, he announced that he was horny, and went to go set up porn.  I
followed him in, and he was pulling down his pants to sit down.  This time,
I sat next to him, and he didn't complain.

We mostly jerked off watching the screen.  And like always, neither of us
came close to touching each other.  But when we were getting closer, I
suggested something we had done a while ago.

"Contest?"

He immediately replied, "Sure!"

I was referring to a distance contest.  Earlier in the year, we found out
that I can shoot a lot farther than him.  It was a fair contest, too.
We're about the same height and we were rubbing for about the same amount
of time.

We went over to the hardwood hallway, lined up our toes, and resumed
stroking.

After a minute, he asked, "Ready?"

I was close, so I agreed.

He sighed and started squirting out on the floor, and the sight of him
cumming pushed me over the edge.  I grunted and blew my load too.

Last time, he hadn't done much more than dribble his cum on the floor.  But
this time, his globs were out a foot in front of him!  Mine were still more
than twice as far out, but he was clearly proud of his improvement.

"You've been practicing!"

"Yup.  May even beat you next time!"

I was sure he wouldn't, but he laughed and we went to go watch some TV for
the afternoon.  I felt much better having him as a friend today.

But before I knew it, Tuesday rolled around again.  And this time, I had a
plan.

In the morning, I again took the time to jerk off, so that I would be the
right amount of horny by the end of the day.

And at the end of the day, I wasn't as unlucky as last time.  It was just
Sam and James at his house when I arrived.  And this time, there was no
mention of tutoring.  They were just waiting for me to show up and fuck his
girlfriend on his bed.  They both knew that the tutoring was just an excuse
now, but she didn't know that he knew that.

I was working with the theory that she was the sort of slut who, despite
enjoying manipulating guys, was really turned on by being told what to do.
So this time, I worked on being more in control, like you sometimes see in
porn (yes, the same porn I was complaining about earlier!).

"Get naked," I said directly to her.

She did as I directed, leaving her clothes on the floor.

Meanwhile, James was watching us intently, unlike previous times.  His
wide-eyed expression reminded me of a boy seeing porn for the first time.

After removing her bra, she stared at me waiting for what was next.

I pulled my shirt off in one move and tossed it aside, and pushed my pants
and boxers off in another smooth move.  She rubbed her legs together a bit
as I stood in front of her naked.  My dick was just as impressive soft as
hard, and she was anticipating it.

I reached out with a condom package, and she took it.  Without saying
anything, she knew that I was giving that job to her this time.  She knelt
in front of me, and started to stroke me until I got hard.  My dick didn't
put up a fight though.  She looked as hot naked as she did clothed at
school.  Her body was perfect and trim.  Her tits were just big enough to
bounce during sex, and they were perfectly symmetrical.  And she kept her
pussy completely shaved.  Honestly, she looked like one of those porn
models that welcome you to porn websites.  And she was on her knees, trying
to get me hard.

She started to roll the condom on, the wrong way first.  I think most boys
buy condoms and try them on long before they have a chance at sex, and they
learn the right way to put it on.  But a girl couldn't!  In a second she
was rolling it on correctly.  By the time she had it all the way on, I was
harder than she had ever seen it.

I gently pushed her back onto the bed, and climbed over her.

I kept up the masculine bit and lowered my voice just a little.  "You
horny?"

All she said was, "Mm Hm."

But I wanted more than that.  So I just stayed right over her with my
raging hardon and tried again, "Do you want it?"

"Yes!"

"Beg for it and I'll give it to you!"

"Please put your cock in me, sir!  I need it so bad!!"

Sir?  No time to analyze that now!  She was going with it so I positioned
the head of my cock at her entrance.  I started pushing in, much slower
than I usually did.  I was giving her time to appreciate my length.

She shivered as my trimmed pubes touched her bare skin, and I reached the
deepest point in her I could.  I pulled out slowly, intending to increase
my speed constantly as I fucked her.

After several slow strokes, I added a new move.  I hunched my back a little
bit and started fucking her a little more shallowly so I could reach her
nipples.  I took the nipple on the right into my mouth and started sucking
on it roughly, and licking around it.

"Ohhhh..." she let me know that she enjoyed it.

I kept up the rough sucking, then switched and gave the other one the same
treatment.

Soon after, I stopped that and went back to maximum penetration with each
thrust, and picked up speed.  She was breathing faster.

"Tell me you like it," I said.

She quickly responded, "I love it!  I need this!"

And I could tell!  She was getting even wetter.  Each stroke was getting
easier and smoother.  And shortly, my own arousal started to catch up to
hers.  The pleasure radiating out of my dick was getting more intense.
This fuck wasn't gonna last forever.

I reached down above my dick and started jiggling her clit.  It wasn't easy
to do it at the angle, but I could definitely tell that she enjoyed it.

"How's that?" I asked, as macho as I could muster.

"It's amazing, sir!  I've never felt this way before!" she replied,
breathily.

Whatever she was doing, it didn't sound totally realistic.  But I could
tell she wasn't lying.  She was starting to moan every time I shoved my
cock into her.  "Oh... oh... oh... oooh... oh..."

I was thrusting pretty fast now, and rubbing her clit as hard as I could
from my angle.  I could feel my own orgasm approaching.  If I was gonna get
to my goal, I was gonna have to put everything I had into this!

"Are you my bitch?"  I asked aggressively without a pause in thrusting.

"Yes!  I'm your bitch!  Fuck me like the slut I am!"

I took her up on that, and started pistoning as hard as I could.  As I was
slamming into her, I knew I wasn't gonna last long, and I couldn't do much
with her clit now.

But then she started to moan louder, and then screamed.
"Ohhhhhh... yeeeaaaahhhhh... ohhhh... MMMMMMMMM AHHH AHHH AHHH AHHH!"

I felt her pussy squeeze a little, and I was right on the edge, pistoning
into her.  A second squeeze, and I was cumming too, and I couldn't do it
quietly either.

"Ahhh Unnhh UNNHH UNNHH fffff... AHHHH!" I moaned loudly at the same time
as her.

My thrusts slowed as we moved though our orgasms.

We stayed nearly still for a minute, my dick still deep inside her, before
I pulled out.  And when I did, the condom was literally dripping from her.

Normally after sex, her bitch mode returned immediately.  This time, she
forgot about it for a couple minutes.  But it still returned.

She looked over at James, who still had that wide-eyed expression.  "Your
services are not needed today."

He didn't like doing that for her, but she still managed to make it mean.

She dressed, and as she was leaving the room, she told him, "Get some
lessons from him before our next time."

Victory!  My revenge was a complete success!  Not only did I give his
girlfriend an orgasm in front of him, but she took the time to humiliate
him after it!

After she left, I had to ask, "Have you really never given her an orgasm?"

He said quietly, "No."  After a second, he clarified, "Not while I was
still fucking.  How the fuck did you do that?"

"What do you mean?  You watched the whole thing!"

"Yeah, but I fuckin' do all that shit."

"Well, you can't fuck her with my dick."  I was standing in front of him,
so it was at eye level for him.

He just sighed, and I left.

That Saturday, my JOB was over again, and we were enjoying ourselves.  He
was really getting off on my used condom, after I told him that a
cheerleader had orgasmed around it.  And I got a text from James.  She
skipped his sex day, and he was pathetically asking whether I owed him
another handjob.  I replied simply "not yet", and went back to jerking off
to the porn.  I cummed harder than usual, thinking back to what I had done
with his girlfriend.


Fucking five chapters!  Keep up the feedback!  jacksta@ymail.com.